This week, our host Erica Wenger wraps up an incredible Season 4 of Dear Twentysomething ! 🎉 Join us as we reflect on some of the most memorable guests and standout moments from the season. Erica shares her takeaways, favorite conversations, and the wisdom we’ve gathered along the way. Plus, a sneak peek at what’s in store for Season 5! Whether you’ve been with us since the beginning or just discovered the show, this episode is the perfect way to celebrate how far we’ve come and where we’re hea...
May 06, 2025•4 min•Season 4Ep. 133
This week, we chat with Melanie Strong! Mel started her career as a first grade teacher and journalist. A fateful interview with her running hero Joan Benoit Samuelson led to a long-shot interview for an entry level job at Nike. She spent 17 years there, where she led several businesses including Nike Women and Nike Skateboarding, and worked on the launch of the Nike Running and Training Club apps. Mel started angel investing and advising early stage founders in 2017, and left Nike to co-found v...
Apr 29, 2025•54 min•Season 4Ep. 132
This week, we chat with Lauren Berson-Sugarman! Lauren Berson is an executive turned entrepreneur with 20 years of experience building brands, products, and communities across a diverse set of industries. Lauren is the founder and CEO of Conceive, a digital health platform aiming to change fertility outcomes and experiences through community, evidence-based education, and coaching. Her focus on this problem and intention behind the company is deeply personal. She welcomed her daughter into the w...
Apr 23, 2025•52 min•Season 4Ep. 131
This week, our host, Erica Wenger, shares practical and honest advice on how to navigate your career in your 20s—drawing from her own journey through college, her first job, working in VC, podcast hosting, and more! In this episode, Erica breaks down the big things that helped her build momentum early in her career—from actively absorbing information to putting herself in rooms with the right people. Whether you're in business or not, the lessons shared here are widely applicable. Erica talks ab...
Apr 15, 2025•20 min•Season 4Ep. 130
This week, we chat with Courtney Powell! Courtney is COO and Managing Partner at 500 Global, tasked with helping the firm scale globally and explore new opportunities across markets. She is responsible for operations across the team to pursue 500 Global’s mission of uplifting people and economies through entrepreneurship. She is also on the advisory council of Harvard Kennedy School’s Mossavar-Rahmani Center for Business and Government supporting more effective interactions between the public an...
Apr 08, 2025•54 min•Season 4Ep. 129
This week, we chat with TJ Taylor! TJ has spent over a decade as an early stage consumer operator—most recently Employee #1 at Raya and founding team member at Dispo. His areas of focus has been GTM and Growth (product, marketing, and community led). Currently, he is running consultancy and advisory company for consumer startups. Additionally, he’s serving as a Venture Scout for the consumer team at Headline (looking at early stage consumer tech companies). Follow Us! TJ Taylor: @tjtaylr Erica W...
Apr 01, 2025•55 min•Season 4Ep. 128
This week, our host, Erica Wenger, shares a number of practical and unconventional tips on how to fundraise effectively as an early-stage founder! In this episode, Erica breaks down the fundraising process beyond the typical advice, offering insights on how to approach investors, craft a compelling narrative, and stand out in a crowded market. She challenges common misconceptions about fundraising and highlights creative strategies founders can use to secure capital—whether through unconventiona...
Mar 26, 2025•21 min•Season 4Ep. 127
This week, we chat with Siqi Chen! Siqi is the founder and CEO of Runway, a next generation FP&A platform that makes finance actually understandable and accessible to the entire team. As an operator and founder, he served as the CEO of Sandbox VR (a16z), VP of Product and Growth at Postmates (later acquired by Uber), CEO of Hey, Inc (Google-funded, acquired by Postmates), Head of Product at Zynga (IPO 2011) and CEO of Serious Business (funded by Lightspeed, acquired by Zynga). In addition to...
Mar 18, 2025•45 min•Season 4Ep. 126
This week, we chat with Troy Osinoff! Troy is the Co-founder of JUICE, a digital marketing agency credited by Facebook as being a top 1% agency with clients such as L’Oreal, Super Coffee, Solidcore & Bartstool Sports. Prior to JUICE, Troy helped a bankrupt shoe company reach profitability, grew a Grammy-winning recording studio, created a viral media site called Make A Dare (featured on Dr. Phil), co-founded a media company with 1.7M visitors daily ($0 paid promotion), and created a viral Tu...
Mar 11, 2025•41 min•Season 4Ep. 125
This week our host, Erica Wenger, chats about her most recent essay: Getting Off The Alphabet Train! On this episode Erica dives into her newest essay which challenges the traditional VC funding model. Getting off the Alphabet Train explores the shift away from traditional VC funding, where startups chase valuations through seed and Series rounds. Instead, a new wave of “elephant” companies is prioritizing profitability, community-driven growth, and long-term sustainability over constant fundrai...
Mar 05, 2025•13 min
This week, we chat with Jacqueline Blackburn! Jacqueline is a Principal at Decisive Point and leads the acceleration portfolio. Jacqueline graduated from the United States Naval Academy and led forward-deployed teams in the Naval Explosive Ordnance Disposal Community. She was responsible for training and building small teams for no-fail missions in the Middle East and Africa. Prior to Decisive Point, she spent several years at J.P. Morgan working closely with founders and building out their earl...
Feb 25, 2025•50 min•Season 4Ep. 123
This week, our host, Erica Wenger, goes solo to break down the secrets to hosting a standout curated tech event. From timing it just right to crafting the perfect guest list. Erica shares insider tips on how to create an event that’s both high-value and high-impact. You’ll learn what makes a great tech gathering, how to foster meaningful conversations, and the key elements that separate a forgettable meetup from an exclusive must-attend experience. Whether you’re planning your first event or loo...
Feb 18, 2025•14 min•Season 4Ep. 122
This week we chat with Grace Clarke! Grace Clarke is the founder of GGC Consulting, redefining how brands grow by building community-powered flywheels, not funnels, growing brands like Graza, Madewell, Jones Road, Estee Lauder, Target, Google. She is also the founder of GraceAI, a marketing strategy and calendar generator (basically an AI clone of her brain). She also runs the Gen Z Board of Directors, an insights network of young people, is an artist, and splits her time between New York and Pa...
Feb 11, 2025•42 min•Season 4Ep. 121
This week we chat with Eli Weiss! Eli has spent the last decade building and operating early-stage startups. He is particularly known for his work around the convergence of Customer Experience and Customer Retention at DTC brands such as Jones Road Beauty, OLIPOP, and many more. After years of building brands that put the customer first, he’s switched to the tech side to help build the future of Customer Retention at Yotpo. Follow us! Eli Weiss: @eliweisss Yotpo: @yotpo Erica Wenger: @erica_weng...
Feb 04, 2025•57 min•Season 4Ep. 120
This week we chat with Brett Perlmutter! Brett is the founder of Bulletpitch. Bulletpitch is redefining venture through media. Their flagship product is a publication that highlights and performs high-level diligence on top-tier startups. The publication has become a staple for 1000s of investors and has helped companies raise millions of dollars by being featured. Bulletpitch also has an events arm, where they have hosted everything from intimate breakfasts, pitch events, and large gatherings o...
Jan 28, 2025•46 min•Season 4Ep. 119
This week we chat with Nihal Mehta! At Eniac, they call Nihal the human Rolodex, thanks to the thousands of connections he has made with some of the world’s top companies and brands. He developed many of these connections (and scar tissue!) over the past 20+ years while founding five startups: Philly2nite -> UrbanGroove -> Chapter 7 bankruptcy; ipsh! -> acquired by Omnicom (NYSE: OMC); buzzd -> LocalResponse -> acquired by BlueCava. Early in his career, Nihal honed his ability to ...
Jan 21, 2025•41 min•Season 4Ep. 118
This week our host, Erica Wenger, takes a step back to reflect on the highs, lows, and lessons of 2024 while looking ahead to the opportunities of 2025. In this episode, she shares her personal process for year-end reflection, breaking it down into eight fool-proof buckets to help you identify what went well, what didn’t, and how to grow. From celebrating wins to recalibrating for the future, she provides actionable insights and tools to help you visioncast your best year yet. Whether you're wra...
Jan 14, 2025•10 min•Season 4Ep. 117
This week we chat with Dennis Hegstad! Dennis is an experienced entrepreneur and founder, having co-founded LiveRecover, an SMS marketing company for Shopify merchants that scaled to thousands of users and drove over $100 million in additional revenue. He also founded OrderBump, a Shopify app for upsells, which he quickly grew and sold within just 100 days. Currently, Dennis is the co-founder of Vigilance, and Internet Research Unit. Follow us! Dennis Hegstad: @dennishegstad Internet Research Un...
Dec 17, 2024•52 min•Season 4Ep. 116
This week we chat with Lisa Mayer! Lisa Mayer is the co-founder & CEO of Boss Beauties, a next gen tech company backed by Serena Ventures, the $100M+ venture fund founded by world class athlete Serena Williams. Boss Beauties inspires & elevates the next generation of women & girls to be everything they want to be through technology, content, and education. Boss Beauties was first born in emerging tech and they have had massive traction in the web3 space, launching multiple collection...
Dec 10, 2024•44 min•Season 4Ep. 115
This week we chat with Mac Reddin! Mac Reddin is the Founder and CEO of Commsor. At Commsor he's focused on building tools to enable companies to embrace Go-to-Network, a more sustainable way to grow compared to traditional direct Go to Market motions. Prior to Commsor he bootstrapped and exited various businesses across gaming, fashion, and software. Follow us! Mac Reddin: TheTeaGuns Commsor: @Commsor Erica Wenger: @erica_wenger Dear Twentysomething: @deartwentysomething...
Dec 03, 2024•51 min•Season 4Ep. 114
This week we chat with Ben Lang! Ben has spent his life hopping between New York, Tel Aviv, and San Francisco. He is a builder, former founder, and community guy, always in multiple places at one time. He was an early member of the Notion team, where he led community for nearly 5 years. He actively makes angel investments and advises a few select startups. He’s helping world-class talent discover what’s next through next play . Follow us! Ben Lang: @benln next play: @nextplayso Erica Wenger: @er...
Nov 26, 2024•43 min•Season 4Ep. 113
This week we chat with Nik Sharma! Nik is the CEO of Sharma Brands, a strategic initiatives firm working with a wide range of brands to help grow and scale revenue across digital platforms. Nik is one of AdWeek’s Young & Influential, Forbes 30 under 30, Business Insider's up and coming Investors to Watch, and an investor and advisor to some of the fastest-growing brands in commerce. Follow us! Nik Sharma: @mrsharma Sharma Brands: @sharmabrands Erica Wenger: @erica_wenger Dear Twentysomething...
Nov 19, 2024•51 min•Season 4Ep. 112
This week we chat with Sieva Kozinsky! Sieva is a founder of Enduring Ventures, a long-term holding company that buys wonderful businesses and holds them forever. Sieva is a lifelong entrepreneur who started Enduring Ventures with Xavier Helgesen, taking inspiration from Warren Buffett's Berkshire Hathaway model. Together with investors, they own stakes in over 20 companies, including Somewhere.com, Scribe Media, and Abstract. Sieva is a founder of Enduring Ventures, a long-term holding company ...
Nov 12, 2024•50 min•Season 4Ep. 111
This week we chat with Liz Wessel! Liz Wessel is a Partner at First Round Capital, a pre-seed and seed venture fund, based in San Francisco. Prior to joining First Round, she was a Visiting Group Partner at Y Combinator, where she worked directly with over 110 early-stage startups. Liz has also been investing as an angel since 2016, backing over 60 startups, including Ramp, ScaleAI, Ro, Artera (fka WELL Health), FreeWill, Snackpass and others. Before becoming a full-time investor, Liz was the co...
Nov 05, 2024•53 min•Season 4Ep. 110
This week we chat with Casey Lewis! Casey is a youth trends expert and brand consultant. Formerly an editor at Teen Vogue, MTV, and New York Magazine. She now writes After School, a trends newsletter read by 45,000+ people, and helps companies reach Gen Z. Follow us! Casey Lewis: @caseymlewis Erica Wenger: @erica_wenger Dear Twentysomething: @deartwentysomething...
Oct 29, 2024•53 min•Season 4Ep. 109
This week our host, Erica Wenger, chats about her most recent essay: Elephants in the Wild! On this episode Erica dives into her newest essay which draws a parallel between the Ironman Triathlon and successful startups, focusing on the qualities that create strong, long-lasting brands. Using the Ironman community as an example, Erica highlights how Elephants—those built on social attraction, mission-driven growth, and public transparency—foster deep loyalty through identity, community, and share...
Oct 22, 2024•20 min•Season 4Ep. 107
This week we chat with Jason Yeh! Jason Yeh is the Founder of Adamant, a fundraising strategy and investor relations firm dedicated to making capital raising less painful for founders and fund managers around the world. As a formal and informal advisor to startups, he’s helped companies raise over $300MM in capital - first as an investor at Greycroft Partners and afterwards as a founder where he led multiple fundraises. His previous company Tape sold to Hustle in 2020. Jason is a graduate of the...
Oct 15, 2024•48 min•Season 4Ep. 107
This week we chat with April Underwood! April Underwood is co-founder and Managing Director of Adverb Ventures, a venture capital firm investing in early-stage technology startups launched in 2023. In addition, April is a member of the boards of directors for Zillow Group and Eventbrite, and a co-founder of the #ANGELS angel investing collective through which she backed over 50 companies as an angel investor. April brings 20 years of experience building software to her role as an investor. Until...
Oct 08, 2024•54 min•Season 4Ep. 106
This week we chat with Andrew Gazdecki! Andrew is a 4x founder with 3x exits, former CRO, and founder of Acquire.com. Gazdecki has been featured in The New York Times, Forbes Wall Street Journal, Inc. Magazine, and Entrepreneur Magazine, as well as prominent industry blogs such as Mashable, TechCrunch and VentureBeat. Follow Us! Andrew Gazdecki: @agazdecki Acquire.com: @acquiredotcom Erica Wenger: @erica_wenger Dear Twentysomething: @deartwentysomething...
Oct 01, 2024•36 min•Season 4Ep. 105
This week we chat with Sara Mauskopf! Sara Mauskopf is the CEO and Co-founder of Winnie , a leading marketplace for daycare and preschool helping millions of parents across the United States. Parents use Winnie to discover high-quality local daycares and preschools and learn all about their programs including detailed descriptions, photos, tuition information, licensing status, availability data and more. Child care providers use Winnie to get the tools and support to grow their business. Sara h...
Sep 24, 2024•52 min•Season 4Ep. 104
